Chemical synthesis of sulfated oligosaccharides with a β-D-Gal-(1→3)-[β-D-Gal-(1→4)-(α-L-Fuc-(1→3)-β-D-GlcNAc-(1→6)]-α-D -GalNAc sequence

Jie Xia; T. Srikrishnan; James L. Alderfer; R. K. Jain; Conrad F. Piskorz; Khushi L. Matta

doi:10.1016/S0008-6215(00)00211-1

Chemical synthesis of sulfated oligosaccharides with a β-D-Gal-(1→3)-[β-D-Gal-(1→4)-(α-L-Fuc-(1→3)-β-D-GlcNAc-(1→6)]-α-D -GalNAc sequence

Jie Xia
, T. Srikrishnan
, James L. Alderfer
, R. K. Jain
, Conrad F. Piskorz
, Khushi L. Matta

Department of Chemical and Biological Engineering

Roswell Park Cancer Institute

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

Abstract

The syntheses of two sulfated pentasaccharides: β-D-Gal6SO₃Na-(1→3)-[β-D-Gal-(1→4)-α-L-Fuc-(1→3)-β-D-GlcNAc-(1→6) ]-α-D-GalNAc→OMe (1) and β-D-Gal6SO₃Na-(1→3)-[β-D-Gal-(1→4)-α-L-Fuc-(1→3)-β-D-GlcNAc6SO₃Na -(1→6)]-α-D-GalNAc→OMe (2) by using Lewis(X) trisaccharides 12 and 16 as glycosyl donors are described. Sulfated oligosaccharides 1-2 and intermediate compounds are fully characterized by 2D ¹H-¹H DQF-COSY and 2D ROESY experiments. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	561-577
Number of pages	17
Journal	Carbohydrate Research
Volume	329
Issue number	3
DOIs	https://doi.org/10.1016/S0008-6215(00)00211-1
State	Published - Nov 17 2000

Keywords

2D DQF-COSY
2D ROESY
Chemical synthesis
Crystallography
Sulfated oligosaccharides

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10.1016/S0008-6215(00)00211-1

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@article{e0de798217db439b8b9a9f9fe5b2a953,

title = "Chemical synthesis of sulfated oligosaccharides with a β-D-Gal-(1→3)-[β-D-Gal-(1→4)-(α-L-Fuc-(1→3)-β-D-GlcNAc-(1→6)]-α-D -GalNAc sequence",

abstract = "The syntheses of two sulfated pentasaccharides: β-D-Gal6SO3Na-(1→3)-[β-D-Gal-(1→4)-α-L-Fuc-(1→3)-β-D-GlcNAc-(1→6) ]-α-D-GalNAc→OMe (1) and β-D-Gal6SO3Na-(1→3)-[β-D-Gal-(1→4)-α-L-Fuc-(1→3)-β-D-GlcNAc6SO3Na -(1→6)]-α-D-GalNAc→OMe (2) by using Lewis(X) trisaccharides 12 and 16 as glycosyl donors are described. Sulfated oligosaccharides 1-2 and intermediate compounds are fully characterized by 2D 1H-1H DQF-COSY and 2D ROESY experiments. (C) 2000 Elsevier Science Ltd.",

keywords = "2D DQF-COSY, 2D ROESY, Chemical synthesis, Crystallography, Sulfated oligosaccharides",

author = "Jie Xia and T. Srikrishnan and Alderfer, \{James L.\} and Jain, \{R. K.\} and Piskorz, \{Conrad F.\} and Matta, \{Khushi L.\}",

year = "2000",

month = nov,

day = "17",

doi = "10.1016/S0008-6215(00)00211-1",

language = "English",

volume = "329",

pages = "561--577",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier Ltd",

number = "3",

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TY - JOUR

T1 - Chemical synthesis of sulfated oligosaccharides with a β-D-Gal-(1→3)-[β-D-Gal-(1→4)-(α-L-Fuc-(1→3)-β-D-GlcNAc-(1→6)]-α-D -GalNAc sequence

AU - Xia, Jie

AU - Srikrishnan, T.

AU - Alderfer, James L.

AU - Jain, R. K.

AU - Piskorz, Conrad F.

AU - Matta, Khushi L.

PY - 2000/11/17

Y1 - 2000/11/17

N2 - The syntheses of two sulfated pentasaccharides: β-D-Gal6SO3Na-(1→3)-[β-D-Gal-(1→4)-α-L-Fuc-(1→3)-β-D-GlcNAc-(1→6) ]-α-D-GalNAc→OMe (1) and β-D-Gal6SO3Na-(1→3)-[β-D-Gal-(1→4)-α-L-Fuc-(1→3)-β-D-GlcNAc6SO3Na -(1→6)]-α-D-GalNAc→OMe (2) by using Lewis(X) trisaccharides 12 and 16 as glycosyl donors are described. Sulfated oligosaccharides 1-2 and intermediate compounds are fully characterized by 2D 1H-1H DQF-COSY and 2D ROESY experiments. (C) 2000 Elsevier Science Ltd.

AB - The syntheses of two sulfated pentasaccharides: β-D-Gal6SO3Na-(1→3)-[β-D-Gal-(1→4)-α-L-Fuc-(1→3)-β-D-GlcNAc-(1→6) ]-α-D-GalNAc→OMe (1) and β-D-Gal6SO3Na-(1→3)-[β-D-Gal-(1→4)-α-L-Fuc-(1→3)-β-D-GlcNAc6SO3Na -(1→6)]-α-D-GalNAc→OMe (2) by using Lewis(X) trisaccharides 12 and 16 as glycosyl donors are described. Sulfated oligosaccharides 1-2 and intermediate compounds are fully characterized by 2D 1H-1H DQF-COSY and 2D ROESY experiments. (C) 2000 Elsevier Science Ltd.

KW - 2D DQF-COSY

KW - 2D ROESY

KW - Chemical synthesis

KW - Crystallography

KW - Sulfated oligosaccharides

UR - https://www.scopus.com/pages/publications/0034680713

U2 - 10.1016/S0008-6215(00)00211-1

DO - 10.1016/S0008-6215(00)00211-1

M3 - Article

C2 - 11128585

AN - SCOPUS:0034680713

SN - 0008-6215

VL - 329

SP - 561

EP - 577

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 3

ER -

Chemical synthesis of sulfated oligosaccharides with a β-D-Gal-(1→3)-[β-D-Gal-(1→4)-(α-L-Fuc-(1→3)-β-D-GlcNAc-(1→6)]-α-D -GalNAc sequence

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